Moonlight Cruise on Alyosha
An Experience Unlike Anything Else
There are only about five or six nights each summer where everything falls into place for this trip. The moon has to be right. The wind has to be light. The skies have to be clear. And the sea has to be gentle. When all of that comes together—and it doesn’t always—you get to experience something truly magical: sailing under the stars and a full moon on the Atlantic Ocean.
This is Ocean City’s most exclusive sailing experience—and for good reason. The conditions have to align perfectly, and when they do, you’re in for something you’ll remember for years.
This is easily our favorite experience to offer, and a personal favorite of your captain. There’s something about being out on the water at night, under a full moon, that connects you to every sailor who has ever gone to sea in search of opportunity. It’s an unforgettable commune with nature—quiet, beautiful, and unlike anything else you’ll do on vacation.
We also have other smooth sailing trips here.
Where We Go
If conditions are right for the Atlantic, that’s where we’ll be—out on the open ocean under the moon and stars. If the Atlantic is too rough but the evening is still beautiful, we’ve had incredible moonlight sails behind Assateague Island in the flat, calm waters of Sinepuxent Bay. This will always be the captain’s call based on conditions, and either way, it’s a special night.
This is a 2-hour trip, and we cap it at just 8 passengers to make sure everyone has room to spread out and really take it in. We recommend ages 16 and up for this experience—this is an evening best enjoyed with a beverage in hand and nowhere to be.
What to Expect on Your Moonlight Cruise
When this trip happens, it is magical. The engine goes off, the sails fill, and suddenly it’s just the sound of the water against the hull and the glow of the moon on the sea. You’ll find yourself reflecting on all of the sailors who have bravely gone to sea in search of opportunity—and you’ll understand, in a way you can’t from shore, why they did it.
The experience is different from daytime sailing in every way. Your eyes adjust to the darkness. The rigging creaks softly above you. If you’re lucky, you might see bioluminescence trailing in the wake—tiny points of light in the water that glow when disturbed. The moon path stretches across the sea, and you realize how small boats really are out here.
On the Atlantic, expect open water, stars in every direction, and the kind of silence that’s hard to come by. Behind Assateague, the water is flat and calm, the moon reflects off the bay, and the wild island sits dark and quiet beside you. Both are unforgettable.
Who Is This Evening Cruise For?
Couples looking for a date night they’ll never forget. Friends who want to do something completely different. Anyone who’s ever looked up at a full moon and thought, “I wonder what that looks like from the middle of the ocean.” This trip is intimate, peaceful, and a little bit magical—it’s for anyone who wants to slow down and experience something real.
Looking for a daytime romantic experience? Try our Sunset Cruise —another intimate sailing experience perfect for couples and celebrations.
A Note on Motion Sickness
This trip only goes out in gentle conditions, so motion sickness is rarely an issue. And if the captain opts for the behind-Assateague route, the water is flat and calm—no worries at all. If you’ve been hesitant about sailing because of seasickness concerns, this is actually one of the best trips to try.
Weather & Cancellation
This sunset cruise is weather dependent. If Captain Steve feels there’s any risk given the day’s conditions—including a forecast that doesn’t look promising—the trip will be cancelled and you’ll receive a full refund, no questions asked.
We need a minimum of 4 people for this sunset cruise to run. If we fall short of the minimum, we’ll refund anyone who booked—but don’t let that discourage you from booking. We almost always hit the minimum, and if we don’t, we’ll find another time that works for you.
What to Bring on Your Moonlight Cruise
It’s nighttime on the water, so bring an extra layer. And bring an “appropriate” quantity of your favorite beverage—we’ll leave the definition of “appropriate” up to you. This is your night.
Alyosha has bottled water for all guests. Restrooms (“heads”) are aboard for customer use—just keep in mind the toilets on a sailboat are a little more sensitive than the ones on land.
Common questions about our moonlight cruises in OCMD
The Moonlight Cruise is offered on select nights throughout the summer when the full moon coincides with ideal sailing conditions. There are typically only five or six nights each summer when everything falls into place—clear skies, light winds, a full moon, and gentle seas. Trips are scheduled around the full moon cycle and require perfect weather conditions to go out.
The Moonlight Cruise runs less than 50% of the time it’s scheduled, and that’s by design. This trip only happens when conditions are perfect—light winds, clear skies, and a gentle sea. If conditions aren’t right, your trip will be fully refunded with no questions asked. Think of it as a perfect guarantee: either you get spectacular moon viewing and peaceful sailing conditions, or you get your money back.
If weather conditions aren’t perfect for the Moonlight Cruise, you’ll receive a full refund—no questions asked. Our staff will be in communication with you throughout the day leading up to the scheduled departure to keep you updated on conditions. We only run this trip when conditions are ideal for a safe and magical moonlight sailing experience.
We recommend ages 16 and up for the Moonlight Cruise. This is an intimate, peaceful experience best enjoyed with a beverage in hand and nowhere to be. The trip is capped at just 8 passengers to ensure everyone has room to spread out and take in the night sky and moonlit water.
The route depends on conditions. If the Atlantic Ocean is calm and clear, that’s where we’ll be—out on the open water under the moon and stars. If the Atlantic is too rough but the evening is still beautiful, we’ve had incredible moonlight sails behind Assateague Island in the flat, calm waters of Sinepuxent Bay. The captain makes the final call based on conditions, and either route offers an unforgettable moonlight sailing experience.
Motion sickness is rarely an issue on the Moonlight Cruise because this trip only goes out in gentle conditions. If the captain opts for the behind-Assateague route, the water is flat and calm with no worries at all. If you’ve been hesitant about sailing because of seasickness concerns, this is actually one of the best trips to try.
It’s nighttime on the water, so bring an extra layer—temperatures can drop once the sun goes down, especially earlier in the season. Wear comfortable, casual clothing and non-slip shoes. Sunglasses aren’t needed, but you might want a light jacket or sweatshirt. And bring an appropriate quantity of your favorite beverage—this is your night to relax and take in the moonlit sea.
Moonlight Cruise dates are posted on our booking calendar when the full moon schedule aligns with available sailing windows. Visit our booking page to see upcoming Moonlight Cruise dates and reserve your spot. Trips are limited to 8 passengers and fill up quickly. Departures are from Olde Towne Marina at 307 Dorchester Street in Ocean City, Maryland.
New to sailing with us? We have several different options, you can visit our Assateague Trips or our Ocean Trips. Each has several options to suit your needs.
Getting to Our Ocean City Sailing Charters
Trips depart promptly at the scheduled time from Olde Towne Marina (307 Dorchester Street, Ocean City, MD 21842), right next to Oyster & Scales in downtown OC. Parking can be limited, so plan to arrive a few minutes early. You can’t miss Alyosha—we’re the only sailing vessel around.